WO2004024172A1 - Methode d'extraction et de purification des principes actifs de la tige de lonicera japonica, et leur utilisation dans des medicaments anti-inflammatoires et analgesiques - Google Patents

Methode d'extraction et de purification des principes actifs de la tige de lonicera japonica, et leur utilisation dans des medicaments anti-inflammatoires et analgesiques Download PDF

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Publication number
WO2004024172A1
WO2004024172A1 PCT/KR2003/001851 KR0301851W WO2004024172A1 WO 2004024172 A1 WO2004024172 A1 WO 2004024172A1 KR 0301851 W KR0301851 W KR 0301851W WO 2004024172 A1 WO2004024172 A1 WO 2004024172A1
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WO
WIPO (PCT)
Prior art keywords
active constituents
inflammatory
honeysuckle
sweroside
stem
Prior art date
Application number
PCT/KR2003/001851
Other languages
English (en)
Inventor
Wie-Jong Kwak
Yong-Baik Cho
Chang-Kyun Han
Hee Jae Shin
Keun Ho Ryu
Hunseung Yoo
Hae In Rhee
Original Assignee
Sk Chemicals, Co., Ltd.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from KR1020020055106A external-priority patent/KR100834966B1/ko
Priority claimed from KR1020020058494A external-priority patent/KR100796384B1/ko
Application filed by Sk Chemicals, Co., Ltd. filed Critical Sk Chemicals, Co., Ltd.
Priority to US10/527,139 priority Critical patent/US7314644B2/en
Priority to EP03795473A priority patent/EP1536811A4/fr
Priority to JP2004535252A priority patent/JP2006510592A/ja
Priority to AU2003260985A priority patent/AU2003260985B2/en
Publication of WO2004024172A1 publication Critical patent/WO2004024172A1/fr
Priority to HK06101294.5A priority patent/HK1081115A1/xx
Priority to US11/652,360 priority patent/US20070111955A1/en

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • A61K36/35—Caprifoliaceae (Honeysuckle family)
    • A61K36/355—Lonicera (honeysuckle)
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]

Definitions

  • the present invention relates to an extraction and purification method of active constituents from honeysuckle (Lonicer japonica Thunb.) and its use, more particularly to an extraction and purification method of active constituents including sweroside from honeysuckle stem (stem of honeysuckle where leaves are removed) by removing tannins, hardly soluble flavonoids, saponins, and the like.
  • honeysuckle stem stem of honeysuckle where leaves are removed
  • tannins tannins, hardly soluble flavonoids, saponins, and the like.
  • the honeysuckle (Lonicera japonica Thunb.) is a semi-evergreen viny shrub that grows naturally at the feet of mountains or levees in the range of an altitude of 50 to 600 meters in Japan, China and Korea. Its flower bud (honeysuckle flower) and stem (honeysuckle stem) are used as herbal medicines for promotion of urination, detoxification, hemostasis, blood purification, treatment of tumor, edema treatment, cold, diarrhea, emesis, and the like [Illustrated Book of Korean Flora,
  • hydrolyzable tannins such as caffeoylquinic acid, methyl caffeate, chlorogenic acid and iso-chlorogenic acid, and iridoid glycosides such as loganin, sweroside, vogeloside and epi-vogeloside are known as effective active constituents contained in honeysuckle stem.
  • Most conventional researches have been centered on honeysuckle flower and honeysuckle leaves. It should be noted that honeysuckle stem has a different distribution of constituents from honeysuckle leaves or honeysuckle flower.
  • honeysuckle leaves or honeysuckle flower major constituents of honeysuckle leaves or honeysuckle flower are flavonoids, such as lonicerin, rhoifolin and ochnaflavon, triterpene saponins having hederagenin or oleanolic acid as non-sugar constituent, and various hydrolyzable tannins.
  • flavonoids such as lonicerin, rhoifolin and ochnaflavon
  • triterpene saponins having hederagenin or oleanolic acid as non-sugar constituent and various hydrolyzable tannins.
  • honeysuckle leaves and honeysuckle flower are greater in tannins and hardly soluble flavonoids than honeysuckle stem. In the acute toxicity test for injections, they confer more toxicity than honeysuckle stem even at low contents, and provide poor analgesic and anti-inflammatory effect.
  • honeysuckle stem stem of honeysuckle where leaves are removed
  • tannins hardly soluble flavonoids, saponins, and the like have been removed
  • sweroside the effective active ingredient of the active constituents
  • Fig. 1 is a graph that shows medicinal effects of the active constituents depending on their contents.
  • the present invention provides a method for preparing active constituents from honeysuckle stem, which have superior anti-inflammatory and analgesic activity, safety and stability.
  • the present invention also provides an anti-inflammatory and analgesic drug comprising the active constituents.
  • the present invention also provides an anti-inflammatory and analgesic drug comprising sweroside.
  • the present invention relates to a method extracting and purifying active constituents and sweroside from honeysuckle by removing tannins, hardly soluble flavonoids, saponins, and the like.
  • active constituents have significantly better anti-inflammatory and analgesic effect, are safer and more stable than the conventional active constituents obtained from honeysuckle flower or honeysuckle leaves, and also include sweroside which is an effective active ingredient of anti-inflammatory and analgesic drug.
  • Active constituents and sweroside are extracted from honeysuckle stem and purified by the following method.
  • a honeysuckle stem sample is reflux-extracted with about 7 to 10 volumes of distilled water for 2 to 3 hours, and then filtered.
  • the residue is collected and reflux-extracted with about 5 to 7 volumes of distilled water for 2 to 3 hours.
  • Thus obtained liquid is filtered and combined with the above filtrate, concentrated under reduced pressure, and filtered again, so that its volume becomes about 1 to 3 times (v/w) with reference to the herb weight.
  • v/w v/w
  • the water-saturated low grade alcohol is added and stirring is carried out for about 10 to 20 minutes at 30 to 50 rpm.
  • the water-saturated low grade alcohol layer is filtered and concentrated under reduced pressure to obtain primary active constituents.
  • the water- saturated low grade alcohol to be used is prepared by adding distilled water to low grade alcohol, such as propyl alcohol and butyl alcohol, and stirring followed by sedimentation. The process of layer separation is carried out for 2 to 3 times.
  • a column chromatography is carried out for the primary active constituents using polyamide resin, polyvinylpyrrolidone resin, and the like in order to remove unwanted materials and detect effective ingredient.
  • the filler is used in 1 to 10 volumes (w/w) of the water-saturated low grade alcohol layer. Two three volumes of 50% (v/v) methanol and methanol to the filler volume are eluted, and then the distilled water solvent is eluted by step-gradient method.
  • the secondary active constituents obtained by eluting the active constituents with distilled water had much less aromatic organic acids, tannins and flavonoids, and showed better medicinal effect, significantly reduced toxicity, increased solubility and improved blood stability.
  • a column chromatography is carried out again for the secondary active constituents using ODS (octadecylsilane) resin.
  • ODS octadecylsilane
  • 2 to 3 volumes of solvent to the resin volume is eluted by the step-gradient method while increasing the methanol content by 10% (v/v).
  • the polyamide resin or polyvinylpyrrolidone resin is used in 20 to 50 volumes for the weight of the purified primary active constituents.
  • the active constituents obtained by eluting 20 to 30% (v/v) methanol showed the best anti-inflammatory and analgesic effect.
  • Analysis of the active constituents revealed that iridoid substances, such as sweroside and loganin are major active ingredients.
  • the sweroside content was 15.1 to 72.1 wt%, and the loganin content was 13.9 to 41.4 wt%.
  • the active constituents obtained by eluting 20 to 30% (v/v) methanol has the highest sweroside content.
  • Another column chromatography was carried out for these active constituents to separate sweroside represented by the following Chemical Formula 1:
  • the sweroside obtained by the present invention can be prepared into treatment drugs by the methods known in the pharmaceutical circle. And, it can be administered orally or parenterally alone or along with a pharmaceutically acceptable carrier, a forming agent, a diluent, etc. Particularly, it can be prepared in the form of powder, granule, tablet, capsule, syrup, skin ointment or injection drug.
  • the human dosage of the active constituents or sweroside of the present invention can be selected considering the absorptivity of the active ingredient in the body, inactivation rate and excretion rate, age, sex and physical status of the subject, severity of the disease to be treated, and so forth.
  • the active constituents or sweroside are administered from 1 to 200 mg a day for an adult.
  • the drug may be administered according to specialized method, if required by the experts' opinion.
  • the drug may be administered several times a day, preferably
  • the drug composition may be administered orally or non-orally.
  • the drug When the drug is to be administered parenterally, it can be administered through veins, muscles, rectum or skin.
  • honeysuckle stem Because the active constituents of honeysuckle stem have superior anti- inflammatory and analgesic effect and desirable solubility, acute toxicity and blood stability, they are well suited for the injection drug.
  • honeysuckle honeysuckle with stem and leaves
  • honeysuckle leaves and honeysuckle stem were taken at Yeongcheon, Gyeongsangbuk-do, Korea in July 1999.
  • the samples were dried in the shade and reflux-extracted with 7 volumes of distilled water for 2.5 hours, and then filtered.
  • the residue was then collected and reflux-extracted with 7 volumes of distilled water for 2.5 hours.
  • liquid was filtered and combined with the above filtrate, concentrated under reduced pressure, and filtered again, so that its volume became about 2 times (v/w) with reference to the herb weight.
  • equal volume of water-saturated n-butyl alcohol was added and the mixture was stirred for 15 minutes at about 30 rpm.
  • the alcohol layer was filtered and concentrated under reduced pressure to obtain primary active constituents. Then, a column chromatography was carried out for obtaining the purified fraction using polyamide resin (CAS NO. 63428-83-1). The resin amount was 5 volumes of the sample. Two volumes of 50% (v/v) methanol and methanol were eluted, and then the distilled water solvent was eluted by step-gradient method to obtain secondary active constituents.
  • Rate of inflammation [Thickness of inflamed (right) ear - Thickness of normal (left) ear] / [Thickness of normal ear] 100
  • honeysuckle stem As shown in Table 1, the active constituents of honeysuckle stem showed best anti-inflammatory and analgesic activity.
  • Example 2 Comparison of medicinal effect of active constituents obtained from honeysuckle stem
  • the secondary active constituents obtained from honeysuckle stem included no compounds like aromatic organic acids, tannins and flavonoids, and had a greater content of active ingredient than the primary active constituents.
  • Example 3 Comparison of medicinal effects of active constituents obtained from honeysuckle stem
  • Example 1 The procedure of Example 1 was carried out by replacing polyamide resin with polyvinylpyrrolidone resin (CAS NO. 25249-54-1).
  • the secondary active constituents of honeysuckle stem prepared in Example 1 were concentrated under reduced pressure to obtain a powder.
  • Another column chromatography was carried out for the powder using ODS resin (YMC*GEL ODS-A 12 nm, S-150 m or ODS-AM 12 nm, S-50 m or ODS-AQ 12 nm, S- 50 m).
  • ODS resin YMC*GEL ODS-A 12 nm, S-150 m or ODS-AM 12 nm, S-50 m or ODS-AQ 12 nm, S- 50 m.
  • Three volumes of resin was used and 20% (v/v) methanol was eluted to obtain the final active constituents.
  • Table 5 Contents of sweroside and loganin depending on habitat and time of
  • Example 1 final active constituents of honeysuckle stem and primary active constituents of honeysuckle stem, honeysuckle leaves and whole body of honeysuckle
  • Example 4 final active constituents of Example 4 were put in a test tube (Physiological salt solution and distilled water (100 % hemolysis) control groups were also prepared).
  • the test tube was incubated in a bath kept at 37 ° C for 15 minutes, and then placed at room temperature for 45 minutes. Lastly, after centrifuge at 2500 rpm for 2 minutes, the upper layer was analyzed at 540 nm.
  • Example 8 Determination of anti-inflammatory effect of sweroside
  • Example 9 Determination of analgesic effect of sweroside
  • honeysuckle stem and sweroside in the amount of 1.0 g/kg, 1.5 g/kg and 2.0 g/kg, were administered through the tail veins of SD rats (body weight: 120 to 170 g, 5 male and female rats for each administration dose, SLC, Japan), respectively, which had been fasted for 4 hours.
  • the rats were observed for 30 minutes at first, and then observed at 30 minutes intervals with naked eyes. Death rate, general symptoms and weight change were observed for 2 weeks after administration.
  • An autopsy was conducted to identify presence of any abnormalities of organs.
  • the lethal dose of the active constituents of honeysuckle stem and sweroside was both over 5.0 g/kg for oral administration (no dead rats observed), and over 2.0 g/kg for intravenous injection (no dead rats observed).
  • 2.0 g/kg was intravenously injected, the rats showed increased respiration counts and decreased activity for about 10 minutes, which were restored soon. No other symptoms were observed, and there was no change in weight due to administration.
  • the autopsy result showed no abnormalities as is the case with the control groups.
  • honeysuckle stem or sweroside The active constituents of honeysuckle stem or sweroside was prepared into a tablet with the following composition: Active ingredient 160 mg
  • honeysuckle stem or sweroside The active constituents of honeysuckle stem or sweroside was prepared into syrup with the following composition:
  • honeysuckle stem or sweroside The active constituents of honeysuckle stem or sweroside was prepared into an injection with the following composition: Injection ampule: Active ingredient 20 mg
  • honeysuckle stem or sweroside The active constituents of honeysuckle stem or sweroside was prepared into an injection with the following composition:
  • Injection ampule Active ingredient 50 mg
  • honeysuckle stem or sweroside The active constituents of honeysuckle stem or sweroside was prepared into an injection with the following composition: Injection ampule: Active ingredient 100 mg
  • the active constituents of honeysuckle stem or sweroside was prepared into an ointment drug the following composition: Active ingredient 5 g Liquid paraffin 10 g
  • the active constituents of the present invention obtained from honeysuckle stem have significantly increased solubility and blood stability as compared to those of the conventional active constituents. Further, they are shown to have superior analgesic and anti-inflammatory effect, safety and stability. Also, sweroside of the present invention obtained from honeysuckle stem has very superior medicinal effect and shows little toxicity, thus being very suitable for an anti-inflammatory and analgesic drug.

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Abstract

L'invention porte sur une méthode d'extraction et de purification des principes actifs de la Lonicera Japonica, (chèvrefeuille) et sur leur utilisation, et plus particulièrement sur une méthode d'extraction et de purification de principes actifs, dont le sweroside, de la tige de la Lonicera Japonica mais sans les feuilles de manière à éliminer les tannins, les flavonoïdes faiblement solubles, les saponines et autres. Les principes actifs ainsi obtenus ont une activité anti-inflammatoire et analgésique accrue, sont plus sûrs et plus stables que les extraits usuels de fleurs et de feuilles, et contiennent du sweroside, ingrédient actif des médicaments anti-inflammatoires et analgésiques.
PCT/KR2003/001851 2002-09-11 2003-09-08 Methode d'extraction et de purification des principes actifs de la tige de lonicera japonica, et leur utilisation dans des medicaments anti-inflammatoires et analgesiques WO2004024172A1 (fr)

Priority Applications (6)

Application Number Priority Date Filing Date Title
US10/527,139 US7314644B2 (en) 2002-09-11 2003-09-08 Extraction and purification method of active constituents from stem of Lonicera japonica thunb., its usage for anti-inflammatory and analgesic drug
EP03795473A EP1536811A4 (fr) 2002-09-11 2003-09-08 Methode d'extraction et de purification des principes actifs de la tige de i lonicera japonica /i , et leur utilisation dans des medicaments anti-inflammatoires et analgesiques
JP2004535252A JP2006510592A (ja) 2002-09-11 2003-09-08 スイカズラ（ＬｏｎｉｃｅｒａｊａｐｏｎｉｃａＴｈｕｎｂ．）茎の活性成分の抽出および精製方法、その消炎鎮痛剤への用途
AU2003260985A AU2003260985B2 (en) 2002-09-11 2003-09-08 Extraction and purification method of active constituents from stem of Lonicera japonica Thunb., its usage for anti-inflammatory and analgesic drug
HK06101294.5A HK1081115A1 (en) 2002-09-11 2006-01-27 Extraction and purification method of active constituents from stem of lonicera japonica thunb., its usage for anti-inflammatory and analgesic drug
US11/652,360 US20070111955A1 (en) 2002-09-11 2007-01-11 Extraction and purification method of active constituents from stem of Lonicera japonica Thunb., its usage for anti-inflammatory and analgesic drug

Applications Claiming Priority (4)

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KR10-2002-0055106 2002-09-11
KR1020020055106A KR100834966B1 (ko) 2002-09-11 2002-09-11 인동등으로부터 유효활성성분을 함유하는 인동등 분획물의 제조방법 및 상기 인동등 분획물을 함유한 소염, 진통 주사제 조성물
KR10-2002-0058494 2002-09-26
KR1020020058494A KR100796384B1 (ko) 2002-09-26 2002-09-26 스웨로사이드를 유효성분으로 함유하는 소염, 진통제 조성물

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US (2) US7314644B2 (fr)
EP (1) EP1536811A4 (fr)
JP (1) JP2006510592A (fr)
CN (1) CN100544744C (fr)
AU (1) AU2003260985B2 (fr)
HK (1) HK1081115A1 (fr)
WO (1) WO2004024172A1 (fr)

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CN106831910B (zh) * 2017-02-17 2019-11-01 中日友好医院 一种马钱苷原料药的制备方法

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US20070111955A1 (en) 2007-05-17
US7314644B2 (en) 2008-01-01
JP2006510592A (ja) 2006-03-30
US20060014240A1 (en) 2006-01-19
AU2003260985B2 (en) 2009-09-03
EP1536811A1 (fr) 2005-06-08
HK1081115A1 (en) 2006-05-12
CN1684699A (zh) 2005-10-19
EP1536811A4 (fr) 2009-07-29
CN100544744C (zh) 2009-09-30

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